EP-A-44,209 discloses herbicidal sulfonamides of formula ##STR1## wherein R is H, F, Cl, Br, NO.sub.2, CF.sub.3, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy;
R.sub.1 is H, Cl or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.2 is H or CH.sub.3 ; and PA1 L is, among other values, CO.sub.2 R.sub.10, CONR.sub.3 R.sub.4, CN, Cl, Br, NR.sub.3 R.sub.4, S(O).sub.n R.sub.7, SO.sub.2 NR.sub.3 R.sub.4 and OR.sub.9. PA1 R.sub.9 and R.sub.10 are, among other values, H or CH.sub.3 ; and PA1 R.sub.11 is COR.sub.24 or a C.sub.1 -C.sub.4 alkyl group substituted with, among other values, CN, NO.sub.2, OH, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkoxy, NR.sub.12 R.sub.13 and SO.sub.2 NR.sub.15 R.sub.16. PA1 R.sub.1 is C.sub.1 -C.sub.3 alkyl; and PA1 R.sub.2 is C.sub.2 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyloxy, C.sub.3 -C.sub.6 alkenylthio, C.sub.3 -C.sub.6 alkynylthio, OCH.sub.2 CH.sub.2 OCH.sub.3, OCH.sub.2 CH.sub.2 SCH.sub.3, CH.sub.2 F, CHF.sub.2, OCF.sub.2 H, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, OCH.sub.2 CH.sub.2 Cl, C.sub.2 -C.sub.6 alkyl substituted with 1-3 atoms of F or Cl or C.sub.1 -C.sub.4 alkyl substituted with C.sub.1 -C.sub.2 alkoxy or C.sub.1 -C.sub.2 alkylthio; PA1 A is alkynyl, alkyl which is unsubstituted or substituted by halogen, alkoxy, alkylthio, alkylsylfinyl, alkylsulfonyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl, or alkenyl which is unsubstituted or substituted by the substituents given above for alkyl, or A is a phenyl or benzyl group; PA1 E is methine; PA1 X is oxygen, sulfur, or a sulfinyl or sulfonyl bridge; PA1 Z is oxygen or sulfur; PA1 R.sub.1 is hydrogen, alkyl or alkoxy; PA1 R.sub.2 is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, amino, alkylamino, di-alkylamino, cycloalkyl or alkoxyalkyl, R.sub.3 is hydrogen, halogen, alkyl, alkenyl, haloalkyl, --CO--NR.sub.8 R.sub.9, --CN, --COR.sub.10, --NR.sub.1 R.sub.7 or --NR.sub.1 --COR.sub.12 ; PA1 R.sub.4 is hydrogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, halogen, or alkoxyalkyl; PA1 R.sub.5 is independently selected from the same groups as R.sub.3 or --X--R.sub.6 ; PA1 R.sub.6 and R.sub.7 are each alkyl, alkenyl or alkynyl; PA1 R.sub.8 and R.sub.9 independently of one another are each hydrogen, alkyl, alkenyl or alkynyl; PA1 R.sub.10 is hydrogen, alkyl or haloalkyl; PA1 R.sub.11 is hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, phenyl or benzyl; and PA1 R.sub.12 is the same as R.sub.1 but independent thereof. PA1 R.sub.3 and R.sub.4 independently of one another denote hydrogen or (C.sub.1 -C.sub.4)-alkyl; PA1 R.sub.5 denotes hydrogen, halogen, (C.sub.1 -C.sub.4)-alkylamino, di(C.sub.1 -C.sub.4)-alkylamino, (C.sub.1 -C.sub.4)-alkyl which is optionally mono-substituted or poly-substituted by halogen, (C.sub.1 -C.sub.3)-alkoxy or (C.sub.1 -C.sub.3)-alkylthio, or denotes (C.sub.1 -C.sub.4)-alkoxy, (C.sub.1 -C.sub.4)-alkylthio, allyloxy or propargyloxy; PA1 R.sub.6 and R.sub.7 independently of one another denote hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-halogenoalkyl, halogen or (C.sub.1 -C.sub.2)-alkoxy-(C.sub.1 -C.sub.2)-alkyl; PA1 R.sub.8 denotes (C.sub.1 -C.sub.4)-alkyl, (C.sub.2 -C.sub.4)-alkenyl or benzyl; PA1 R.sub.9 denotes (C.sub.1 -C.sub.4)-alkyl which is optionally substituted by CN or (C.sub.1 -C.sub.4)-alkoxycarbonyl, or denotes (C.sub.1 -C.sub.4)-alkoxy; PA1 m denotes the number 1 to 3; PA1 n denotes the number 0 to 2; and PA1 X denotes a methine group or nitrogen. PA1 W is O or S; PA1 R is H or CH.sub.3 ; PA1 R.sub.1 is F, Cl, Br, NO.sub.2, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 haloalkenyl, C.sub.2 -C.sub.4 alkynyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, OCH.sub.2 CH.sub.2 OCH.sub.3, C.sub.1 -C.sub.4 haloalkoxy, C.sub.3 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.4 haloalkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, CO.sub.2 R.sub.3, CONR.sub.4 R.sub.5, SO.sub.2 NR.sub.4 R.sub.5, SO.sub.2 N(OCH.sub.3)CH.sub.3, S(O).sub.n R.sub.6, OSO.sub.2 R.sub.7, C.sub.1 -C.sub.2 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, OH or C.sub.1 -C.sub.2 alkylthio, CH.sub.2 CN, C.sub.6 H.sub.5, ##STR9## R.sub.2 is CH(R.sub.16)CN, CH(R.sub.17)SCN, ##STR10## R.sub.3 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, ##STR11## CH.sub.2 CH.sub.2 Cl, CH.sub.2 CH.sub.2 F, or C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 or SCH.sub.3 ; PA1 R.sub.4 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.5 is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.4 and R.sub.5 may be taken together to form (CH.sub.2).sub.3 or (CH.sub.2).sub.4 ; PA1 R.sub.6 is C.sub.1 -C.sub.3 alkyl, CH.sub.2 CH.dbd.CH.sub.2 or CH.sub.2 C.tbd.CH; PA1 R.sub.7 is C.sub.1 -C.sub.3 alkyl or N(CH.sub.3).sub.2 ; PA1 R.sub.8 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, CH.sub.2 CH.sub.2 Cl, CH.sub.2 CH.sub.2 F, C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 or SCH.sub.3 or C.sub.3 -C.sub.6 cycloalkyl; PA1 R.sub.9 is C.sub.1 -C.sub.2 alkyl; PA1 R.sub.10 and R.sub.11 are independently C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, NHCH.sub.3 or N(CH.sub.3).sub.2 ; PA1 R.sub.12 and R.sub.13 are independently H or C.sub.1 -C.sub.2 alkyl; PA1 R.sub.14 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.15 is H or CH.sub.3 ; PA1 R.sub.16 is H, C.sub.1 -C.sub.2 alkyl or F; PA1 R.sub.17 is H or C.sub.1 -C.sub.2 alkyl; PA1 R.sub.18 is C.sub.1 -C.sub.2 alkyl; PA1 R.sub.19 is H, Si(CH.sub.3).sub.3 or C.sub.1 -C.sub.2 alkyl; PA1 R.sub.20 is H or C.sub.1 -C.sub.2 alkyl; PA1 p is 1 or 2; PA1 n is 0, 1, or 2; PA1 A is ##STR12## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino; PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkynyl, C.sub.3 -C.sub.5 cycloalkyl, azido, cyano, ##STR13## m is 2 or 3; Q.sub.1 and Q.sub.2 are independently O or S; PA1 R.sub.a is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.b and R.sub.c are independently C.sub.1 -C.sub.3 alkyl; PA1 Z is CH, N, CCH.sub.3, CC.sub.2 H.sub.5, CCl or CBr; PA1 Y.sub.1 is O or CH.sub.2 ; PA1 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA1 X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ; PA1 Y.sub.2 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, SC.sub.2 H.sub.5, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA1 Y.sub.3 is H or CH.sub.3 ; PA1 X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl; PA1 Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl; PA1 (1) when X is halogen, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, OCF.sub.2 H or N(OCH.sub.3)CH.sub.3 ; PA1 (2) when X or Y is C.sub.1 haloalkoxy, then Z is CH; PA1 (3) when W is S, then R is H, A is A-1, Z is CH or N, and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or ##STR14## (4) when the total number of carbon atoms of X and Y is greater than four, then the combined number of carbons of R.sub.1 and R.sub.2 is less than or equal to six; PA1 (5) when R.sub.2 is C(O)R.sub.17, then R.sub.1 is other than C.sub.1 -C.sub.4 haloalkyl or C.sub.2 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, OH or C.sub.1 -C.sub.2 alkylthio, and Y is other than cyclopropyl; PA1 (6) when Y is C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.2 -C.sub.5 alkylsulfinylalkyl or C.sub.2 -C.sub.5 alkylsulfonylalkyl, then R.sub.2 is other than CH(R.sub.17)NO.sub.2 ; PA1 (7) X.sub.4 and Y.sub.4 are not simultaneously Cl; and PA1 (8) when R.sub.2 is C(O)R.sub.17 then R.sub.1 is other than SO.sub.2 NR.sub.4 R.sub.5 and SO.sub.2 N(OCH.sub.3)CH.sub.3. PA1 W is O; and PA1 R is H; PA1 E is a single bond; PA1 X is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, Cl, F, Br, I, OCF.sub.2 H, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2l CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; and PA1 Y is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, ##STR15## Z is CH or N; 3. Compounds of Preferred 2 where PA1 R.sub.2 is CH.sub.2 CN, CH.sub.2 N.sub.3, ##STR16## 4. Compounds of Preferred 3 where A is A-1. 5. Compounds of Preferred 4 where R.sub.1 is F, Cl, Br, NO.sub.2, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 alkyl substituted with 1-3 F or Cl or 1 Br, C.sub.2 -C.sub.3 alkenyl, C.sub.2 -C.sub.3 alkenyl substituted with 1-3 F or Cl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkoxy substituted with 1-3 F or Cl or 1-Br, allyloxy, propargyloxy, OC(Cl).dbd.CHCl, CO.sub.2 CH.sub.3, CO.sub.2 C.sub.2 H.sub.5, CO.sub.2 CH.sub.2 CH.dbd.CH.sub.2, CO.sub.2 CH.sub.2 CH.sub.2 Cl, CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3, CONH(C.sub.1 -C.sub.2 alkyl), CONCH.sub.3 (C.sub.1 -C.sub.2 alkyl), SO.sub.2 N(OCH.sub.3)CH.sub.3, SO.sub.2 NH(C.sub.1 -C.sub.2 alkyl), SO.sub.2 N(C.sub.1 -C.sub.2 alkyl).sub.2, S(O).sub.n C.sub.1 -C.sub.3 alkyl, OSO.sub.2 C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 or SCH.sub.3, C.sub.6 H.sub.5 and R.sub.1 --A, R.sub.1 --B, R.sub.1 --C, R.sub.1 --D, R.sub.1 --E, R.sub.1 --F, R.sub.1 --G, R.sub.1 --H, R.sub.1 --I, R.sub.1 --J, R.sub.1 --K, R.sub.1 --L, R.sub.1 --M, R.sub.1 --N, R.sub.1 --O, R.sub.1 --P, R.sub.1 --Q R.sub.1 --R, R.sub.1 --S, R.sub.1 --T, R.sub.1 --U, R.sub.1 --V or R.sub.1 --W; PA1 X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, OCF.sub.2 H or OCH.sub.2 CF.sub.3 ; and PA1 Y is CH.sub.3, OCH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3 or CH(OCH.sub.3).sub.2. PA1 R.sub.1 is F, Cl, Br, NO.sub.2, CH.sub.3, CF.sub.3 C.sub.1 -C.sub.2 alkoxy, allyloxy, OC(Cl).dbd.CHCl, CO.sub.2 CH.sub.3, CO.sub.2 C.sub.2 H.sub.5, CO.sub.2 NHCH.sub.3, CO.sub.2 N(CH.sub.3).sub.2, SO.sub.2 NHCH.sub.3 SO.sub.2 N(CH.sub.3).sub.2, SO.sub.2 CH.sub.3, SO.sub.2 C.sub.2 H.sub.5, OSO.sub.2 CH.sub.3, OSO.sub.2 C.sub.2 H.sub.5, R.sub.1 --A, R.sub.1 --B or R.sub.1 --C.
EP-A-112,803 discloses, in part, herbicidal sulfonamides of formula ##STR2##
South African Patent Application 84/2722 discloses herbicidal sulfonamides of formula ##STR3## wherein A is CR.sub.6 R.sub.7 XR.sub.8, CR.sub.9 R.sub.10 R.sub.11 or CHR.sub.7 SCQR.sub.21 ;
EP-A-162,723 discloses 2,5-substituted herbicidal sulfonamides of formula ##STR4## wherein R is H or CH;
U.S. Pat. No. 4,310,346 discloses herbicidal benzensulfonylureas containing an o-sulfonamide moiety which may contain an optional floating substituent selected from F, Cl, Br, C.sub.1 -C.sub.3 alkyl, NO.sub.2, OCH.sub.3, C(O)R.sub.d, CH.sub.2 OR.sub.d, CF.sub.3, NH.sub.2, NMe.sub.2, CN, CH.sub.2 S(O).sub.n CH.sub.3, S(O).sub.n CH.sub.3, NHC(O)R.sub.d or NHCO.sub.2 R.sub.d ; wherein n is 0, 1 or 2 and R.sub.d is C.sub.1 -C.sub.3 alkyl.
U.S. Pat. No. 4,600,428 discloses N-(cyclopropylpyrimidinyl)-N-aryl-sulfonylyreas of the formula ##STR5## wherein Ar is a phenyl group ##STR6## or a naphthyl group and Q is a group X--A or R.sub.3 ;
South African Patent Application 84/5216 discloses herbicidal sulfonamides of formula ##STR7## in which R.sub.1 and R.sub.2 independently of one another denote hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy or (C.sub.1 -C.sub.4)-alkylthio which are optionally monosubstituted or poly-substituted by halogen, NO.sub.2, (C.sub.1 -C.sub.4)-alkoxycarbonyl, --(C.sub.1 -C.sub.4)--S(O).sub.n --, (C.sub.1 -C.sub.4 -alkyl)--N(R.sub.9 SO.sub.2 --, (C.sub.1 -C.sub.4)-alkenyloxy, (C.sub.1 -C.sub.4)-alkynyloxy, --OSO.sub.2 --(C.sub.1 -C.sub.4)-alkyl, --OSO.sub.2 CF.sub.3, --CONHR.sub.3 or --CON(R.sub.32 ;